Cloud-based storage systems and services (e.g., iCloud drive by Apple®) are becoming prevalent as a means for managing data across various user devices, and can provide users with large amounts of storage space (e.g., 1 TB) to store their data. Generally, user devices tend to have less storage space (e.g., 128 GB) than the amount of storage space offered by the cloud-based storage systems. Typically, users are involved in a process of identifying desired files that need to be kept on a storage device (e.g., a Solid State Drive (SSD)) of the user device. In some cases, there may not be enough storage space remaining in the user device for all the desired files and/or to download additional files, which can degrade the user's overall satisfaction with the process. Consequently, there is a need for an improved system for balancing storage space usage between the user device and the cloud-based storage system.